Formation of pyrrolinium derivatives in the bromination reaction of <Emphasis Type=Italic>N</Emphasis>,<Emphasis Type=Italic>N</Emphasis>-dipropargyl ammonium salts

Bromination of ammonium salts containing two propargyl groups afforded bromine-substituted derivatives of pyrrolinium salts. The reactions of piperidinium and morpholinium analogs resulted in spirocyclic ammonium salts.     

Solution behavior of methyl cellulose mixtures with poly(<Emphasis Type=Italic>N</Emphasis>-vinylformamide) in water and dimethyl sulfoxide

The rheological properties of diluted and moderately concentrated solutions of methyl cellulose mixtures with poly(N-vinylformamide) in water and dimethyl sulfoxide are investigated. Negative deviations of the viscosities of these solutions from the additive values are observed and explained by different mechanisms of solvation of macromolecules with water and dimethyl sulfoxide. Incompatibility of the polymers in a common solvent is discovered. This circumstance leads to the formation of a new system of hydrogen bonds and rearrangement of the structural organization of solutions.     

Synthesis and structure of 2,6-diazidotrichloropyridine <Emphasis Type=Italic>N</Emphasis>-oxide

Pentachloropyridine N-oxide readily reacted with sodium azide in aqueous acetone at room temperature to produce 2,6-diazidotrichloropyridine N-oxide in high yield. The molecular and crystalline structures of the product were studied in detail by X-ray analysis and quantum-chemical calculations. Unusual geometric parameters of the azido groups and reactivity of the diazide were rationalized by the presence of strong intramolecular contacts N … O with an energy of ∼6.1 kcal/mol.     

Syntheses proceeding from <Emphasis Type=Italic>N</Emphasis>-(oxiran-2-ylmethyl)-<Emphasis Type=Italic>N</Emphasis>-ethylaniline

The preparation of N-(oxiran-2-ylmethyl)-N-ethylaniline was developed. The compound was used in the synthesis of new N-derivatives of aromatic amines containing vicinal aminoalcohol moieties.     

Solutions of cellulose and its blends with synthetic polymers in <Emphasis Type=Italic>N</Emphasis>-methylmorpholine-<Emphasis Type=Italic>N</Emphasis>-oxide: Preparation,phase state,structure, and properties

Highly concentrated solutions of cellulose and solutions of cellulose blends with synthetic polymers are prepared via the solid-phase dissolution of cellulose in N-methylmorpholine-N-oxide. The phase state and morphological features of these solutions are studied via DSC and polarization microscopy, and their rheological behavior is considered. Evolution in the structure of cellulose in these systems is investigated at all stages during spinning of oriented fibers from solutions. It is first shown that the addition of synthetic polymers to cellulose makes it possible to control processes of cellulose structuring; to stop them at the stage of mesophase formation; and, thus, to avoid further perfection of the structure and formation of the crystalline phase of cellulose.     

Synthesis and structure of aroylamidines and <Emphasis Type=Italic>N</Emphasis>-arylbenzamidines hydrochlorides

Aroylamidines can be obtained as salts in a reaction of the corresponding arylcarbonitriles with anhydrous ethanol in the presence of dry HCl followed by treating intermediate imidoesters with alcoholic solution of ammonia. N-Arylbenzamidines are obtained by reacting benzonitrile with arylamines in the presence of AlCl₃. The structure of arylamines and the reaction conditions significantly affect the yield of the target product, and sometimes the very possibility of its preparation.     

Regioselective <Emphasis Type=Italic>N</Emphasis>-alkylation of (2-chloroquinolin-3-yl) methanol with <Emphasis Type=Italic>N</Emphasis>-heterocyclic compounds using the Mitsunobu reagent

The Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.     

Reactions of 1-bromo-1-nitro-3,3,3-trichloropropene with <Emphasis Type=Italic>O</Emphasis>- and <Emphasis Type=Italic>N</Emphasis>-nucleophiles

Reactions of 1-bromo-1-nitro-3,3,3-trichloropropene with alcohols, benzidine and o-, m-, and p-phenylenediamines was investigated and the reaction conditions were developed. The alkoxylation and amination products and an unusual nitrogen-containing bis-aziridine were obtained; their structures were characterized by the spectral (IR, ¹H, ¹³C NMR, HMQC, and HMBC) methods.     

Reaction of dialkylphosphites with <Emphasis Type=Italic>N</Emphasis>-alkyl-2-chloraldimines

Reactions of some dialkylphosphorous acids with the N-substituted 2-chloroimines were studied. It was shown that the nature of substituents at the nitrogen and phosphorus atoms in the starting materials affected the structure of the reaction products.     

Reaction of Azidocarboxyethyl Alginic Acid with <Emphasis Type=Italic>N</Emphasis>-Nucleophiles

The acylating ability of azidocarboxyethyl alginic acid in reactions with benzylamine, aromatic amines, and carboxylic acid hydrazides has been studied.     

Synthesis and some transformations of <Emphasis Type=Italic>N</Emphasis>,2,2-trimethyltetrahydro-2<Emphasis Type=Italic>H</Emphasis>-pyran-4-amine

Reaction of 2,2-dimethyltetrahydro-2H-pyran-4-one with aqueous methanamine, followed by reduction of the Schiff base thus obtained with sodium tetrahydridoborate gave N,2,2-trimethyltetrahydro-2H-pyran-4-amine which was subjected to cyanoethylation with acrylonitrile. The resulting 3-(2,2-dimethyltetrahydro-2H-pyran-4-ylmethylamino)propanenitrile was reduced with lithium tetrahydridoaluminate to N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-N-methylpropane-1,3-diamine, and some chemical transformations of the latter were studied.     

Epoxide tethering of polymeric <Emphasis Type=Italic>N</Emphasis>-halamine moieties

Three heterocyclic N-halamine structures containing amine, amide, or both functional groups were immobilized onto cotton fabric through epoxide tethering. The coatings were rendered biocidal upon exposure to dilute household bleach solution. The coatings exhibited superior biocidal functionality with complete inactivation of about 6 logs of Staphylococcus aureus and Escherichia coli O157:H7 within 2–10 min contact time depending on the structure. Moreover, the coatings were quite stable against repeated laundering so that recharging was not even necessary after 50 washing cycles. Stability of the coatings against ultraviolet light exposure was studied with a comparison of the amide- and amine-containing N-halamines.     

Oxidative cyclization of <Emphasis Type=Italic>N</Emphasis>-alkyl-2-arylhydrazonothioacetamides

Oxidative cyclization of N-alkyl-2-arylhydrazono-2-cyanothioacetamides by the action of N-chlorosuccinimide, bromine, or iodine affords 4-cyano-5-imino-1,2,3-thiadiazoles.     

Reaction of methylpheophorbides <Emphasis Type=Italic>d</Emphasis> and <Emphasis Type=Italic>b</Emphasis> with amines

A series of formyl analogs of chlorin e₆ 13-amides were synthesized in high yields by reaction under mild conditions of primary and secondary amines with methylpheophorides b and d. In contrast with the secondary 13-amides, tertiary 13-amides were found as two isomers differing in the orientation of the amide plane relative to the plane of the chlorin ring. Methylpheophorbides b and d were more reactive toward the amines than methylpheophorbide a.     

The reaction of <Emphasis Type=Italic>N</Emphasis>-sulfinyltrifluoromethanesulfonamide with triethylphosphate and triethylphosphite

The reaction of N-sulfinyltrifluoromethanesulfonamide CF₃SO₂NSO with triethylphosphate and triethylphosphite results in N-(trifluoromethanesulfonyl)triethoxyphosphazene CF₃SO₂N=P(OEt)₃, which upon heating is converted into the diethyl ester of N-trifluoromethylsulfonylamidophosphoric acid CF₃SO₂NHP(O)·(OEt)₂. The latter was also prepared by alcoholysis of N-(trifluoromethanesulfonyl)trichlorophosphazene or of potassium salt of dichloroanhydride of N-trifluoromethylsulfonylamidophosphoric acid, or by the reaction of the salt CF₃SO₂NHNa with diethylchlorophosphate. Compound CF₃SO₂N=P(OEt)₃ does not rearrange into the isomeric diethyl ester of N-ethyl-N-(trifluoromethylsulfonyl)amidophosphoric acid CF₃SO₂N(Et)P(O)(OEt)₂, contrary to the statement in the literature on the easy rearrangement of phosphazenes RFSO₂N=P(OEt)₃ into amidates RFSO₂N(Et)P(O)(OEt)₂.